Sodium Carbonate → HCID 67410010, compound

HRID 1401276Notes

Reaction equation

HRID 1401276 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]([CH3:11])[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[C:18]([O:23]C)[CH:17]=[C:16]([O:25]C)[C:15]=2[C@@H:27]1[CH2:31][CH2:30][N:29]([CH3:32])[C@H:28]1[CH2:33][OH:34].Cl.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[C:7]([NH:8][CH:9]([CH3:11])[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[C:18]([OH:23])[CH:17]=[C:16]([OH:25])[C:15]=2[C@@H:27]1[CH2:31][CH2:30][N:29]([CH3:32])[C@H:28]1[CH2:33][OH:34]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 67410296HCID 67410296, compound

Product 1

HCID 67410010HCID 67410010, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of example 64 (0.900 g, 1.98 mmol) and pyridine hydrochloride (2.0 g, 17.30 mmol) was heated at 180° C. for a period of 2.5 hours. The reaction mixture was diluted with methanol (60 mL) and basified with solid Na2CO3 to pH 10. The reaction mixture was filtered, and washed with methanol. The organic layer was concentrated and the residue purified by column chromatography using 0.01% ammonia and 4.5% methanol in chloroform as eluent to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationThe organic layer was concentrated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-b56190f51b184c639cd672f88ffa466d
Source dataset
uspto-grants-2014_12
Patent number
US08906953B2

Reaction notes

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